HCID 131729100, compound → HCID 25218127, compound

HRID 1671426Notes

Reaction equation

HRID 1671426 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:31])([CH3:30])[CH:14]([O:20]CC1C=CC(OC)=CC=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:30])([CH3:31])[CH:14]([OH:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 131729100HCID 131729100, compound

Product 1

HCID 25218127HCID 25218127, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of ethyl (2R/S)-4-{[3-(acetylamino)propyl]sulfonyloxy}-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoate (23c) (0.26 g, 0.56 mmol) and 140 mg of 10 wt.-% of palladium on activated carbon in 20 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC and lyophilization of the solvents, 130 mg (68% yield) of the title compound (23) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.97 (s, 3H), 1.14 (s, 3H), 1.35 (t, J=6.8 Hz, 3H), 2.01 (s, 3H), 2.06-2.13 (m, 2H), 3.13-2.26 (m, 2H), 3.33-3.46 (m, 2H), 3.97 (d, J=8.8 Hz, 1H), 4.04 (s, 1H), 4.17 (d, J=9.2 Hz, 1H), 4.26-4.35 (m, 2H), 5.92 (br. m, 1H) ppm. MS (ESI) m/z: 340.04 (M+H)+, 338.01 (M−H)−. The analytical data was consistent with the proposed structure and the data for the enantiopure compound (22).

Workup

  1. customAfter purification by mass-guided preparative HPLC and lyophilization of the solvents

Sources & evidence

ORD record
ord-ed335863a3234bbb8ba5a6fd10f9ad45
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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